Formic Acid → HCID 86638486, compound

HRID 222831Notes

Reaction equation

HRID 222831 reaction equation
C(N(CC)CC)C.C(O)=O.ClC1C=CC=CC=1.[C:18]([NH:21][CH:22]([C:28](=[O:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:20])[CH3:19]>O>[C:18]([NH:21][C@H:22]([C@H:28]([OH:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7964ChlorobenzeneHCID 8471TriethylamineHCID 86638484Ethyl 2-acetylamino-3-oxooctadecanoate

Product 1

HCID 86638486HCID 86638486, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Triethylamine (1.32 g, 13.05 mmol) and formic acid (350 mg, 7.82 mmol) were added to a chlorobenzene solution (10.0 ml) of RuCl[(R,R)-TsDPEN](p-cymene) complex (17.6 mg, 0.03 mmol) and ethyl 2-acetylamino-3-oxooctadecanoate (1.00 g, 2.61 mmol) synthesized in the same method as Example 1. After the reaction mixture was stirred for 15.5 hours at 40° C., water (10 mL) was added thereto and separation operation was carried out at 40° C. to obtain the organic layer. It was confirmed by comparative analysis of the organic layer with sample product using HPLC that the organic layer contained 0.96 g of the title compound (yield: 96%). Further, anti-form:syn-form was 95:5 and the optical purity of the anti-form was 97% ee.

Workup

  1. customsynthesized in the same method as Example 1
  2. customseparation operation
  3. customwas carried out at 40° C.
  4. customto obtain the organic layer

Sources & evidence

ORD record
ord-357a13b73cd0469e8ed89379bf7c869f
Source dataset
uspto-grants-2012_06
Patent number
US08207370B2

Reaction notes

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